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<h1><a href="https://archiveofourown.org/works/26766829">A First Time to Remember</a> by <a class='authorlink' href='https://archiveofourown.org/users/allforoneandoneforanother/pseuds/allforoneandoneforanother'>allforoneandoneforanother</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>From the 2020 Kinktober Files [1]</td></tr>

<tr><td><b>Category:</b></td><td>The Two Princes (Podcast)</td></tr>

<tr><td><b>Genre:</b></td><td>ABDL, Daddy Kink, Diapers, Dry Humping, Hand Jobs, M/M, Plot What Plot/Porn Without Plot</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-10-02</td></tr>

<tr><td><b>Updated:</b></td><td>2020-10-02</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-18 11:29:34</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,297</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/26766829</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/allforoneandoneforanother/pseuds/allforoneandoneforanother</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>For Kinktober Day 1: First Time</p>
<p>Rupert was nervous about his first time, but even more nervous about what he was wearing for it.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Amir/Rupert (Two Princes Podcast)</td></tr>

<tr><td><b>Series:</b></td><td>From the 2020 Kinktober Files [1]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1951000</td></tr>

<tr><td><b>Comments:</b></td><td>2</td></tr>

<tr><td><b>Kudos:</b></td><td>23</td></tr>

</table>

<a name="section0001"><h2>A First Time to Remember</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>To say Rupert was nervous was an understatement. After the initial shock of him marrying a man had worn off, his mother was relatively approving of Amir, saying that at the very least, he was a prince without too much deviant behavior.</p>
<p>Boy, was she wrong.</p>
<p>Rupert had seen porn before, and he had read erotica in the royal library when his mother wasn’t looking. So he had known the basics of sex, and a few kinks. What he hadn’t figured anyone, let alone <em>Amir</em> might have a fetish for, was diapers. More specifically, a diapered <em>partner.</em> And yet, here he was. Waiting for Amir to be done with his shower, wearing a diaper, because Amir had said he’d like that whenever Rupert was ready for sex.</p>
<p>The diaper was soft, and warm, and awkwardly well-fitting on Rupert’s slight frame. He didn’t think that it should have fit this well, even if he knew Amir had taken his measurements for it a couple weeks ago, and placed the order only after he had checked Rupert’s measurements in triplicate. He shifted in it from side to side, wondering how long Amir’s shower might take. He placed his hands between splayed legs and shifted forward—oh. <em>Oh.</em></p>
<p>That had definitely done <em>something</em> to Rupert’s dick. He leaned back and forward again, and again, before swiping at his chin as something wet came into contact with it. Drool. He was <em>drooling</em> because he moved the wrong way in a diaper?</p>
<p>…You know what? If it made Rupert more relaxed in this situation? He would take it. He spread his legs further apart, angled himself a little more towards the en suite, and began to hump.</p>
<p>The motion itself felt weird, sort of like sucking in his stomach and hips before pushing them out again, as waves of pleasure shook him. His eyes fluttered closed, and he moaned. He had masturbated before, but never had it felt quite like <em>this.</em> He could do this all night, if he really felt like it. Just move in and out, back and forth, shoving his diapered dick into the bed…</p>
<p>A quiet sucked-in breath made Rupert’s eyes fly open. He stared, wide-eyed, at Amir, who was looking him over, eyes fixated mostly on Rupert’s diapered groin, and Rupert could swear he saw Amir salivating a little as well. The towel around Amir’s waist did nothing to hide his massive boner. “You—” Amir cleared his throat. “You like this?”</p>
<p>Rupert’s cheeks flared red. “I wasn’t sure I would, but uh…then I moved the wrong way…or sh-should I say the…the <em>right</em> way, and…”</p>
<p>He trailed off into silence. Amir was still staring at him. “God, you looked beautiful, baby. I wish I hadn’t made you stop,” Amir murmured, hands dropping away from the towel and letting it lay on the floor as he walked over to Rupert. He put his hands on Rupert’s shoulders. “Would you be willing to do that a little more for me?”</p>
<p>Rupert was blushing ever harder, but he shyly nodded. “I…I guess…daddy.”</p>
<p>Amir’s eyes widened and Rupert clapped a hand over his mouth. “I’m sorry, I really shouldn’t have—”</p>
<p>“No!” Amir exclaimed. He cleared his throat. “No…I liked it. I was just surprised, baby.”</p>
<p>Rupert looked down and saw that Amir’s own dick was at full attention. “I can see that,” he said, grinning with a cheeky wink.</p>
<p>It was Amir’s turn to turn red, but as he blushed, he <em>growled,</em> and fuck if that wasn’t sexy—“Baby. Hump your diaper for me,” Amir ordered, getting on the bed but giving space for Rupert to move.</p>
<p>Rupert turned towards Amir, and, face red, did the same motion he had done before in the diaper. He jumped a little when he felt something <em>wet</em> and <em>warm</em> enter it. “What? What’s wrong?” Amir asked, surging forward and putting his hands on Rupert’s cheeks.</p>
<p>“I…I don’t know,” Rupert said. He opened the front of the diaper as much as he could, seeing a little pre was dripping down his dick. “Oh, god,” he mumbled. “I’m fine.”</p>
<p>“You’re fine?” Amir echoed disbelievingly.</p>
<p>“Yeah,” Rupert said, biting his lip. “Just really, <em>really</em> turned on.”</p>
<p>Amir blinked, before smirking. “Like it <em>that much,</em> do you?” he asked.</p>
<p>“Shut up and let me put on your nighttime porno,” Rupert snipped.</p>
<p>“Uh…I have lube if you want me to…” Amir trailed off.</p>
<p>“I’ve got a better idea,” Rupert said, guiding Amir’s hand into his diaper. “You get me off, and I’ll get you off.”</p>
<p>“How do you plan to—” Amir was cut off as Rupert put his mouth around Amir’s dick. “You’re flexible.”</p>
<p>Rupert gave Amir a dirty look that roughly equated to <em>shut up and get me off.</em></p>
<p>Amir laughed a little, letting his fingers trail up and down Rupert’s dick. Tickling at every touch, teasing something more as they got to the head and traced circles there. Rupert didn’t know much about sucking cock, but he figured it was sort of like sucking on a lollipop. He sucked, and flicked his tongue around a bit, which made Amir make some <em>interesting</em> noises, and—oh, <em>fuck,</em> that felt good!</p>
<p>“You liked that?” Amir asked as Rupert moaned, cock still in his mouth. “You like me giving you a hand job?”</p>
<p>Amir’s strokes were slow and steady, but he knew all the right places to get Rupert moaning. He took in more of Amir, before slowly grinding into Amir’s hand. Amir laughed, mumbling something about “eager little babies” which had Rupert muffling an embarrassed squeak. Amir’s free hand went up to rest at the nape of Rupert’s neck. “It’s okay, baby. I like this much better knowing that you’re completely ready for it.”</p>
<p>Rupert moved so he was lying on his side, still able to suck off Amir while Amir fondled him. Amir groaned at a particular flick of Rupert’s tongue, so he repeated it, over and over until Amir’s grip on Rupert’s dick was almost painful and he had stopped pumping. Rupert didn’t have time to question why before a salty, bitter substance entered his mouth...out of Amir’s cock. He had successfully gotten Amir off first, from a blowjob no less!</p>
<p>“Oh, god, baby, that felt amazing,” Amir breathed. “Thank you.”</p>
<p>Rupert swallowed the cum and sucked off Amir’s cock with a little <em>pop!</em> sound. “Glad you enjoyed, Daddy,” Rupert said with a little smirk.</p>
<p>“You’re such a smart ass,” Amir said fondly, going back to stroking Rupert.</p>
<p>Rupert practically <em>purrs</em> at the touch. Amir’s fingers, expertly stroking up and around Rupert’s dick feels just a little too good to let go of. His head still in Amir’s lap, Amir praises what a good boy he’s been, how good he’s doing, how Amir loves to see Rupert spread out for him like this and how he’d only <em>dreamed</em> of Rupert looking this perfect.</p>
<p>And when Rupert breathes out a moan and a, “Faster,” Amir obliges, stroking a little faster and a little faster, until Rupert comes loud and hard into the diaper and all over Amir’s hand. Amir pets Rupert’s hair idly as he strokes Rupert through the aftershocks, and eventually, Rupert pulls Amir’s hand out of the diaper. “That was…definitely a first time for the record books,” Rupert laughed.</p>
<p>“That was your first time?!” Amir asked incredulously.</p>
<p>“It <em>wasn’t</em> yours?” Rupert asked back. “I assumed you just had better access to porn than I did.”</p>
<p>“No! I’ve had sex before! You’re a virgin?!”</p>
<p>“I’m not now,” Rupert helpfully pointed out.</p>
<p>Amir groaned. “Shut up! I need to rethink my life for a bit!”</p>
<p>Rupert laughed and got comfortable resting his head in Amir’s lap while Amir babbled on long into the night about re-evaluating his life choices.</p>
<p>
  
</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>Any and all comments welcome.</p></blockquote></div></div>
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